Adhesive applicator tips with improved flow properties

ABSTRACT

An article of manufacture for dispensing an adhesive material, such as a synthetic or semi-synthetic polymerizable or cross-linkable monomer material, includes a container body, and a porous applicator tip having a proximal end that is attached to the container body, and a distal end located away from the container body, wherein the adhesive material is located in the container body in a non-contacting relationship with the applicator tip prior to dispensing the material. A flow pattern of the adhesive material within or on the applicator tip is controlled by providing one or more cuts in the applicator tip to alter flow properties of the adhesive material through the applicator tip.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation-in-part of U.S. patent applicationSer. No. 09/479,059, filed Jan. 7, 2000, the entire disclosure of whichis incorporated herein by reference.

BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention relates to an improved design for an applicator tip,particularly for use with an applicator that dispenses adhesivematerial. In particular, the present invention relates to an applicatortip that exhibits an improved flow pattern of the adhesive material inor through the applicator tip, which allows for more precise placementof the adhesive material and decreased waste of adhesive material.

2. Description of Related Art

Monomer and polymer adhesives are used in both industrial (includinghousehold) and medical applications. Included among these adhesives arethe 1,1-disubstituted ethylene monomers and polymers, such as theα-cyanoacrylates. Since the discovery of the adhesive properties of suchmonomers and polymers, they have found wide use due to the speed withwhich they cure, the strength of the resulting bond formed, and theirrelative ease of use. These characteristics have made theα-cyanoacrylate adhesives the primary choice for numerous applicationssuch as bonding plastics, rubbers, glass, metals, wood, and, morerecently, biological tissues.

It is known that monomeric forms of α-cyanoacrylates are extremelyreactive, polymerizing rapidly in the presence of even minute amounts ofan initiator, including moisture present in the air or on moist surfacessuch as animal (including human) tissue. Monomers of α-cyanoacrylatesare anionically polymerizable or free radical polymerizable, orpolymerizable by zwitterions or ion pairs to form polymers. Oncepolymerization has been initiated, the cure rate can be very rapid.

Medical applications of adhesive compositions include use as analternate or an adjunct to surgical sutures and staples in wound closureas well as for covering and protecting surface wounds such aslacerations, abrasions, bums, ulcers such as stomatitis, sores, andother open surface wounds. When an adhesive is applied to surfaces to bejoined, it is usually applied in its monomeric form, and the resultantpolymerization gives rise to the desired adhesive bond.

However, with the application of adhesive in its monomeric form, due tothe rapid polymerization rate of the monomers, it has been challengingto design effective and commercially viable packaging and dispensingsystems. Such packaging and dispensing systems must counterbalance thecompeting requirements that the monomer not prematurely polymerize, thatthe monomer be easily applied, that the monomer polymerize at a desiredrate upon application, and that the sanitary and/or sterile propertiesof the monomer and applicator—whether real or perceived—be maintained.

In order to meet the above requirements, various dispensing andpackaging systems for adhesives have been proposed. These systemsinclude large bottles with a single applicator, such as a large single-or multi-use brush; small applicators such as small ampoules containingmonomer, for example within an internal frangible vial, that can beexpelled through an integral or replaceable applicator; and the like.However, a problem with many of these applicator systems is that theproduct contains more adhesive material than is necessary for aparticular use. Because of the rapid polymerization rate of themonomers, any unused adhesive is generally discarded, because either theremaining monomer undergoes polymerization, or the monomer polymerizeswithin the applicator to render the applicator unusable.

A disadvantage of some known applicator systems, and particularlyapplicators containing a frangible vial and a porous applicator tip forexpelling the adhesive, is that monomer material may be wasted byfilling the pores of the applicator tip in areas other than the areasused to apply the adhesive. Furthermore, some known applicator tipssuffer from the problem of the monomer being expelled through the entiresurface area of the tip, and even to greater extents in areas other thanthe area used to apply the monomer to the desired substrate. Forexample, large amounts of adhesive become expelled from areas around theperiphery of the applicator tip, where the applicator tip meets theapplicator housing, rather than through the end of the applicator tip,as is often desired. This leads to a further problem of less precisecontrol over the area of application of the monomer to the substrate.

For example, an effective applicator system is disclosed in U.S. Pat.No. 5,928,611 to Leung. This patent discloses an applicator systemgenerally comprising a tube containing a frangible vial of monomericadhesive composition. One end of the tube is sealed, and the other endis closed by an applicator tip comprising a solid support having apolymerization or cross-linking accelerator or initiator for themonomeric adhesive disposed thereon or therein. As shown in FIG. 3 ofthe patent, the applicator tip can be generally dome shaped. Anapplicator device of U.S. Pat. No. 5,928,611 is shown as FIG. 1 herein.The applicator device 100 comprises a cylindrical applicator container200 holding polymerizable and/or cross-linkable material 300 enclosed ina frangible vial 400, and an applicator tip 500 containing apolymerization and/or cross-linking initiator.

However, a difficulty encountered with such a dome-shaped applicatortip, as well as with other solid applicator tips, is that the monomericadhesive material being expelled through the applicator tip tends tofollow paths of least resistance within the tip. That is, as themonomeric adhesive is being expelled, it tends to follow the shortestpaths through the tip, which tend to be around the periphery of the tip,rather than following the longer path through the full length of the tipto the end of the tip. Because the end of the tip is desired to be usedto apply the adhesive, less precise control of placement of the adhesiveis obtained because adhesive becomes expelled through the entire surfaceof the tip. This also tends to result in waste of adhesive material,because all of the adhesive does not exit from the tip at the samelocation.

Applicator devices commercially used for Loctite Product No. 11067-2 andPermatex Product No. ATA-1 contain crushable glass ampoules withinflexible applicators. However, the compositions within the crushableampoules are, in both products, adhesive activators, not the adhesivecomposition itself. In both of these products, the adhesive is containedin a separate dispenser. The dispenser system used for these products isphysically similar to that shown in FIG. 1, except that the applicatortip is rectangular in shape, rather than dome-shaped, and the applicatortip does not contain a polymerization and/or cross-linking initiator foran adhesive material contained in the frangible vial. In this productalso, the above-described problems of wasted material (here, initiator)and less precision in application are also present.

Accordingly, a need exists in the art for improved applicator tipdesigns, which will allow more precise placement of the adhesivematerial. A need also exists in the art for a means to decrease waste ofmonomeric adhesive material, by ensuring that the adhesive materialeither exits at the desired location of the applicator tip, or flows tosuch a desired location on the tip.

SUMMARY OF THE INVENTION

The present invention addresses the above needs by providing applicatortips that possess increased precision in control of placement of theadhesive composition, and a decrease in waste of adhesive. Theapplicator tips of the present invention provide either more uniform orpreferentially controlled paths of resistance within the applicator tip,or provide means for channeling adhesive to an application zone and awayfrom other surface areas of the applicator tip.

A benefit provided by the present invention is thus the ability to applyadhesive material in precise patterns, such as in thin lines. Thepresent invention also allows tailoring of the application pattern basedon alternative designs of the applicator tip, thus allowing flexibilityin application of, for example, from thin lines to thicker lines. Thepresent invention also decreases waste of adhesive material, by allowingeffective use of a greater portion of the volume of adhesive materialcontained within the applicator. In embodiments, it also improves theutilization of polymerization and/or cross-linking initiator and/or ratemodifiers present in the tip.

The present invention provides an article of manufacture for dispensingadhesive material, comprising a container body, and a porous applicatortip having a proximal end that is inserted into or attached to thecontainer body, and a distal end located away from the container body,wherein the adhesive material is located in the container body in anon-contacting relationship with the applicator tip prior to dispensingthe adhesive material.

According to embodiments of the present invention, the applicator tipmay be sectioned, such as by cutting. The sectioning can be formed as,for example, cuts through an entire portion (length, width and/or depth)of the applicator tip, or through only a portion thereof. The sectioningcan also be in the form of channels formed through the bulk material ofthe applicator tip. This sectioning provides for increased flow controlfor application of the material.

In embodiments of the present invention, the applicator tip may beconfigured such that a flow path length ratio A/B is less than 1.5,wherein B represents a length of a shortest flow path of adhesivematerial through the material of the applicator tip to an externalsurface of the applicator tip adjacent the container body, and Arepresents a length of a shortest flow path of the adhesive materialthrough the material of the applicator tip to an external surface of apredetermined application subportion such as the distal end of theapplicator tip. In embodiments, the applicator tip can comprise one ormore grooves that channel adhesive exiting the applicator tip fromperipheral portions of the applicator tip to the distal end of theapplicator tip. In embodiments, the applicator can comprise a protectivecover surrounding at least a part but not all of an area of theapplicator tip extending out of the container body. In embodiments, theapplicator tip can be a hollow porous applicator tip having a proximalend that is inserted into or attached to the container body, and adistal end located away from the container body.

In other embodiments of the present invention, the applicator tip can beformed to include both a first portion that is non-porous orsubstantially non-porous, and a second portion that is porous. In thisembodiment, the flow paths of the adhesive material through theapplicator tip is altered because the adhesive material will flow onlythrough the porous section of the applicator tip.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a side elevational view of an applicator device according tothe prior art.

FIG. 2 is a cross-sectional view of an applicator tip according to theprior art.

FIGS. 3a-3 d are cross-sectional views of applicator tips according tothe present invention.

FIG. 4 is an elevational view of an applicator tip according to thepresent invention.

FIGS. 5a-5 d are elevational views of applicator tips according to thepresent invention.

FIGS. 6a-6 d are elevational views of applicator tips according to thepresent invention.

FIGS. 7a-7 c are elevational views of a luer lock connection forattaching an applicator tip to an applicator body.

FIG. 8 is an elevational view of an assembled applicator device usingthe luer lock system of FIGS. 7a-7 c.

FIG. 9 is a cross-sectional view of a sectioned applicator tip accordingto the present invention.

FIGS. 10a-10 d are cross-sectional views of sectioned applicator tipsaccording to the present invention.

FIGS. 11a-11 b are top-down views of sectioned applicator tips accordingto the present invention.

FIG. 12 is a top-down view of a sectioned applicator tip according tothe present invention.

FIGS. 13a-13 b are top-down views of sectioned applicator tips accordingto the present invention where the sectioning is formed as one or morechannels.

FIGS. 14a-14 b are top-down views of applicator tips according to thepresent invention that include both a porous and a non-porous section.

FIGS. 15a-15 c are elevational views of applicator tips according to thepresent invention that include both a porous and a non-porous section.

DETAILED DESCRIPTION OF EMBODIMENTS

The present invention provides improved applicator tips and applicatordevices that provide significant improvement in the application and useof adhesive material. Such applicator tips can be used, for example, incombination with the adhesive compositions and packaging and dispensingsystems set forth in U.S. Pat. No. 5,928,611, the entire disclosure ofwhich is incorporated herein by reference. Of course, other adhesivecompositions, compatible with the applicators of the present invention,can also be used.

In embodiments of the present invention, an improved applicator tip isprovided wherein the shape and/or construction of the applicator tip isselected so as to control the flow pattern of the adhesive throughand/or on the applicator tip. For example, the shape of the applicatortip can be selected so as to control the flow paths of the adhesivematerial, or the surface of the applicator tip can be configured tochannel adhesive material exiting the applicator tip to a predeterminedlocation, preferably the location used to apply the adhesive.

For example, in the prior art, the lengths of the flow paths of theadhesive are generally longer from the inside of the applicator to theend of the tip than they are from the inside of the applicator to theperiphery or edge surfaces of the applicator tip adjacent the end of thecontainer body. This is shown, for example, in FIG. 2. FIG. 2 is anenlarged scale, cross-sectional view of the prior art applicator tip500. FIG. 2 shows simplified schematics of the flow paths of adhesivematerial through the applicator tip 500 to areas outside of thecontainer body 200. In FIG. 2, the flow paths 501,501′ through theapplicator tip to the end of the tip are longer than, for example, theflow paths 502,502′ to the periphery or external surface of theapplicator tip. In the prior art applicator tip, the flow path length501 is about 11 mm, and the flow path length 502 is about 7 mm, giving aratio of 1.57. Thus, because the flow paths 502,502′ are shorter thanthe flow paths 501,501′, more of the adhesive composition tends tofollow these paths.

One means for controlling and improving flow properties according to thepresent invention is to select the overall shape of the applicator tip.Accordingly, in an embodiment of the present invention, the shape of theapplicator tip is selected to provide flow paths of more uniform length,or even of reversed proportions, from the inside of the applicator tothe periphery of the applicator tip. Examples of such applicator tipsaccording to the present invention are shown in cross-section in FIGS.3a-3 d.

FIG. 3a is a cross-sectional view of an applicator tip 10 according tothe present invention. FIG. 3a shows simplified schematics of the flowpaths of adhesive material through the applicator tip 10 to areasoutside of the container body 19. In FIG. 3a, the lengths of the flowpaths 11,11′ through the material of the applicator tip to an externalsurface of the end of the tip are more closely equal to, for example,those of the flow paths 12,12′ through the material of the applicatortip to an external surface of the applicator tip adjacent the containerbody. That is, as compared to the corresponding flow paths in theapplicator tip of FIG. 2, the flow paths to the end of the tip areshorter in FIG. 3a than in FIG. 2. Thus, because the lengths of the flowpaths 11,11′ are more equal to those of the flow paths 12,12′, there ismore uniform flow of the adhesive through the applicator tip, and theadhesive composition tends to flow or express more uniformly through theapplicator tip.

In embodiments of the present invention, the applicator tip 10 canassume different shapes, as desired. For example, the end of theapplicator tip located nearest the frangible vial, i.e., located withinthe applicator body 19, can have different shapes as shown innon-limiting fashion in FIGS. 3a-3 d. For example, the end of theapplicator tip can be curved or otherwise designed to equilibrate theflow path lengths. As shown in FIG. 3b, the lengths of the flow paths11,11′ through the material of the applicator tip to an external surfaceof the end of the tip are substantially equal to, for example, those ofthe flow paths 12,12′ to an external surface of the applicator tipadjacent the container body. This thus provides a more uniformexpression of the adhesive material through the entire surface of theapplicator tip.

Reversed flow profiles, such as where more adhesive flows through thedistal end of the applicator tip than through peripheral or sideportions of the applicator tip, can also be provided. For example, inthe applicator tip shown in FIG. 3d, the flow paths through the materialof the applicator tip at the distal end are shorter than flow paths tothe remaining surface of the applicator tip.

Alternatively, or in addition, the end of the applicator tip can beshaped so as to accommodate the frangible vial. In these embodiments,the curvature or shape of the end of the applicator tip located nearestthe frangible vial can be designed to more closely match the shape ofthe frangible vial. However, it is preferred that a tight fit betweenthe frangible vial and the internal surface of the applicator tip is notmade, so that there is sufficient room for adhesive material to exit thefrangible vial and enter and pass through the applicator tip. That is,for example, it is preferred that the frangible vial does not enter thetip, which can be accomplished, for example, by providing a frangiblevial that has a diameter greater than the internal diameter of thecurved portion of the applicator tip.

In embodiments of the present invention, it is preferred that the wallsof the applicator tip are of substantially uniform thickness as shown inFIG. 3b. Because the flow pattern of the adhesive through the applicatortip is related to the length of the flow path through the applicatortip, providing substantially equal flow distances helps to provide equalflow throughout the applicator tip. Of course, the applicator tip wallscan be made thinner in desired areas, such as toward the end of theapplicator tip, if desired. This would tend to increase flow of theadhesive through the thinner portions.

Still further, in embodiments of the present invention, the end of theapplicator tip located furthest from the frangible vial, i.e., locatedoutside of the applicator, can have different shapes as shown, forexample, in FIGS. 3a and 3 c. For example, the end of the applicator tipcan have a smooth curvature, as in FIG. 3a, for application of theadhesive material. Alternatively, or in addition, the end of theapplicator tip can be configured so as to provide, for example, moreprecise application of the adhesive material. For example, as in FIG.3c, the applicator tip can have an extension portion thereon, whichdraws the adhesive material to a more defined application area. Thisextension can have any shape and dimension and can, for example, betubular, conical, rounded, or the like.

Likewise, the overall shape of the applicator tip can be any of variousshapes. For example, suitable shapes of the applicator tip are shown inFIGS. 3a-3 d as being a dome-shape. However, the present invention isnot limited to such shapes. Rather, any suitable size and shapeapplicator tip can be used. Generally, the dimensional characteristicsare limited only by the intended use of the applicator, and practicalityconsiderations. Suitable shapes include, but are not limited to,conical, cylindrical, chisel or polygonal shapes. Furthermore, thedesired shapes can be either solid (i.e., having a substantially flat(or planar) bottom end, as shown in FIG. 2), curved (i.e., having acurved bottom end, as shown in FIG. 3a), or hollow (i.e., having asubstantially hollow bottom end, as shown in FIGS. 3b and 3 c). Ofcourse, other geometries can be used, as desired. The length and size ofthe tip can be varied depending on various application parameters. Thetip may be detachable from the applicator body, or may be an integralpart of the applicator.

In the case of using chisel tips, and even other shaped tips, the distalend of the applicator tip can come to a sharp point (such as a chiselshape being formed by two intersecting planar portions). Alternatively,the distal end of the applicator tip can be rounded over, or can have aflattened shape, such as by not having the planes intersect at thedistal end. Still further, as shown in FIG. 5d, the applicator tip canhave other configurations, such as being formed similar to a marker tipto permit more comfortable and natural use of the applicator.

Because it is desired in embodiments of the present invention to controland equalize adhesive flow through the applicator tip, it is preferredin embodiments that the proximal end of the applicator tip, i.e., theend nearest the frangible vial or adhesive material, be shaped so as tohelp achieve such controlled flow. Thus, for example, the proximal endof the applicator tip may be curved, cut-out or hollowed to at leastsome extent. As used herein, “hollow” is meant to refer to a shape ofthe applicator tip where a distinct lumen is present in the applicatortip, as opposed to a porous tip where numerous pores define open spacewithin the applicator tip. Thus a porous tip may or may not also behollow.

In embodiments, the shape of the applicator tip can be formed by anysuitable means or manufacturing process. For example, the hollow shapedapplicator tips can be formed by molding the applicator tip materialinto the desired hollow or other shape, or a solid material can beshaped and/or hollowed, for example, by drilling, filing, boring,cutting, gauging, or the like.

In these embodiments of the present invention, the shape of theapplicator tip is selected so as to control the length of the adhesivematerial flow paths within the applicator tip. By so controlling thelengths of the flow paths, the distribution of adhesive exiting theapplicator tip can be made more uniform, or can establish a specificdesired distribution. Thus, for example, whereas the flow rate ofadhesive in the prior art may have been higher at the periphery or sidesurfaces of the applicator tip than at the distal end of the applicatortip, the applicator tips of the present invention can provide a moreuniform, preferably substantially uniform, flow pattern or expressionthroughout the exposed surface of the applicator tip. In otherembodiments, the shape can be selected such that the flow path lengthwithin the applicator tip is less in the direction to the end or anotherdesired portion of the applicator tip than it is to other areas of theapplicator tip, for example the peripheral or side areas. That is, inthese embodiments, a higher distribution of adhesive is expressed in theapplication area than in the periphery or side portions of theapplicator tip. Such distribution helps to prevent waste of adhesivematerial, and provides for improved precision of application of theadhesive.

According to embodiments of the present invention, a more uniformprofile of adhesive expression is provided in the applicator tip. Thiscan be obtained, for example, by providing an applicator tip wherein thelengths of the shortest flow paths of the adhesive through the materialof the applicator tip are substantially equal over the exposed portionof the applicator tip. For example, the lengths of the flow paths can beapproximated and measured by measuring a shortest distance of travel ofadhesive through the material of the applicator tip to an outer surfaceof the applicator tip.

Thus, for example with reference to FIGS. 3a and 3 b, the shortest flowpaths to an external surface of the applicator tip adjacent theapplicator body are represented by lines 12,12′. Likewise, the shortestflow paths to the distal end of the applicator tip are represented bylines 11,11′. In measuring the lengths of the flow paths, the distancewithin the open or hollowed-out area of the applicator tip is notincluded in the length of the flow path, because this distance is openspace that does not impede adhesive flow. If the length of the shortestflow path through the material of the applicator tip to an externalsurface of the applicator tip adjacent the applicator body is denoted B,and the length of the shortest flow path through the material of theapplicator tip to an external surface of the distal end of theapplicator tip is denoted A, then the value A/B can be used to representa flow path length ratio. In embodiments of the present invention, it ispreferred that the flow path length ratio be less than 1.5, preferablyless than 1.3, more preferably about 1 or less than 1. In embodiments,this ratio is preferably about 1, indicating that the flow paths in theapplicator tip are substantially uniform, and that there are nosignificantly shorter flow paths. In other embodiments, this ratio canbe adjusted so as to be less than 1, such as less than or equal to about0.9, 0.8 or 0.5 or less, indicating that the monomeric adhesive materialencounters shorter flow paths through the material of the applicator tipto the point of application of the adhesive, such as the distal end ofthe applicator tip, than to other areas of the applicator tip.

A further benefit of embodiments of the present invention is that thetotal pore volume of the applicator tip can be decreased. As a result,less of the adhesive material gets trapped in the pores of theapplicator tip, resulting in less waste of material.

In embodiments of the present invention, an alternative or additionalapproach to controlling and improving flow properties is to alter thesurface of the applicator tip, for example to channel adhesive materialexiting the applicator tip to a common location, preferably the locationused to apply the adhesive. One means to accomplish this objective is toform channels in the surface of the applicator tip. These channels willcause adhesive material exiting the applicator tip to flow on thesurface of the tip to the desired area of application. Thus, forexample, where a dome-shaped or cone-shaped or chisel-shaped applicatortip or the like is used, channels can be formed in the surface of thetip to channel adhesive material exiting on the periphery to traveltowards the end of the applicator tip.

FIG. 4 shown an exemplary applicator tip according to this embodiment ofthe invention. As shown in FIG. 4, the applicator tip 20 has formed inthe surface thereof multiple channels or grooves, shown as v-shapedgrooves 21, which converge toward the end of the applicator tip. Ofcourse, such grooves need not be v-shaped, but can assume any desiredshape so long as the function of channeling adhesive material to theapplication area is achieved. For example, the grooves or channels canbe v-shaped, u-shaped, square, semi-circular, semi-oval, or the like. Inaddition, the grooves or channels can be formed such that they areexposed on the surface, or they can be formed to be located beneath thesurface of the applicator tip.

Furthermore, in this embodiment of the present invention, the applicatortip need not be dome-shaped, as shown in FIG. 4. Rather, any suitableapplicator tip shape can be utilized. For example, a particularlysuitable applicator tip shape is a chisel-shape. As shown in FIGS. 5a-5b, the applicator tip can be shaped, for example, as a generally domeshape with two opposing substantially planar faces formed to define achisel tip at the end of the applicator tip. That is, the chisel tip isformed by two intersecting planes in the applicator tip.

When such a chisel shape is used for the applicator tip, theintersecting planes forming the tip can be formed at any desired angle,based for example on the desired use of the applicator. For example, theangle of intersection forming the chisel tip can, in embodiments, beanywhere from 5 to 170°. Preferably, the angle of intersection isbetween about 20 and about 90°, more preferably between about 40 andabout 70°. Of course, values outside of these ranges can be used, inembodiments, as desired.

The tip 30 can also have formed in the surface thereof multiple channelsor grooves, as described above and shown as v-shaped grooves 31, whichconverge at the chisel tip end of the applicator tip. Of course, suchgrooves need not be v-shaped, but can assume any desired shape asdescribed above so long as the function of channeling adhesive materialto the application area is achieved. FIGS. 5a-5 c also show a centralinterior portion of the applicator tip 30 hollowed out, as shown bydashed lines 32. As described above, such design is optional, and can bepresent or not, as desired. Thus, as shown in FIG. 5d, the centralportion can be solid.

As also shown in FIGS. 5a-5 b, the grooves formed in the surface of theapplicator tip can be parallel to each other, or can be offset at adesired angle. For example, as shown in FIG. 5a, the grooves 31 can begenerally parallel to each other, so that adhesive material travellingthrough the bulk applicator tip is channeled to the chisel end of theapplicator tip. However, as shown in FIG. 5b, the grooves can be offset(i.e., non-parallel) by a desired amount. This may be desirable, forexample, where it is known that a larger amount of adhesive materialpasses through the central portion of the applicator tip as compared tothe outer portions of the applicator tip. By making the grooves 31non-parallel, the adhesive material flowing through the central portionof the applicator tip can be dispersed along the width of the chiseltip. This aids in providing a more uniform coating of adhesive materialon the desired surface.

In embodiments of the present invention where the grooves are madenon-parallel on the face of the applicator tip, it is suitable to offsetthe grooves at any desired angle. For example, adjacent lines can beoffset at an angle of, for example, from about 1 to about 15°.Preferably, the adjacent grooves are offset at an angle of from about 2to about 10°, more preferably from about 3 to about 7°.

Furthermore, this embodiment of the present invention is not limited tothe chisel shape shown in FIGS. 5a-5 b. Rather, any suitable shape canbe used to achieve particular results in use of the applicator. Forexample, where chisel shapes are used, the shape, width, and slope ofthe chisel shape can be adjusted to provide different results. Forexample, a wide chisel tip can be provided where a wide area ofapplication is desired, while a narrow chisel tip can be provided wherea thin or narrow area of application is desired. Alternatively, the tipcan be provided in other shapes, such as conical shapes, pyramidalshapes, and the like, where the end of the application tip either comesto a point, is rounded over, or is flattened.

Although FIGS. 5a, 5 b and 5 d show the applicator tip as containingonly three grooves on the visible face of the applicator tip, theinvention is not so limited. Rather, one or more grooves can be formedon each face of the applicator tip. Such grooves can be either separatedby a planar (or curved) surface, as in FIGS. 5a, 5 b and 5 d, or thegrooves can be located continuous and adjacent to each other, as shownin FIG. 5c. Furthermore, although the grooves are shown as being placedonly on the planar faces of the chisel-shaped tip, the present inventionis not limited to such embodiments. Rather, if desired, the grooves canadditionally, or alternatively, be placed on non-planar portions of theapplicator tip. Such placement could further channel the exitingadhesive composition to the desired point of application.

In these embodiments of the present invention, the shape of theapplicator tip and the number and placement of grooves on the surface ofthe applicator tip are also selected so as to alter the effectivedistribution of adhesive material on the surface of the applicator tip.By providing grooves on the surface of the applicator tip, the effectsof gravity, surface tension and capillary action act to draw the exitingadhesive material from the non-application areas of the application tipto the application area of the applicator tip. Thus, for example,whereas the adhesive distribution on the surface of the applicator tipin the prior art may have been higher at the periphery of the applicatortip, the applicator tips of the present invention can provide a higherquantity of adhesive material at the application area, and lesserquantities of material on the remaining surface of the applicator tip.Accordingly, the travel of the adhesive material is effectivelychanneled or “focused” to the application area. Such channeling helps toprevent waste of adhesive material, and provides for improved precisionof application of the adhesive material.

In embodiments of the present invention, the flow pattern of adhesivematerial from the applicator tip can be altered by blocking flow fromdesired portions of the applicator tip. Thus, for example, if it isdesired that adhesive material exits only through the end of theapplicator tip, and not through peripheral portions, such flow patterncan be accomplished by altering the design of the applicator tip toblock flow through such undesired areas. This can be accomplished, forexample, by altering the physical structure of surface areas of theapplicator tip, such as by filling the pores of such areas with amaterial that will prevent flow through those areas, or by covering theareas with a separate material to prevent flow.

As used herein, the term “cover” is used to refer to any suitable meansfor preventing adhesive material from exiting through desired portionsof the applicator tip. Thus, as will be described below, a “cover”includes physically separate components that are placed on or attachedto the applicator tip to block adhesive flow, can be a coating or layerapplied to the surface of the applicator tip to block adhesive flow, orcan be the result of a method of altering at least the surface layer ofthe applicator tip so as to likewise block adhesive flow.

For example, FIGS. 6a-6 d show exemplary embodiments of the presentinvention where the flow pattern is adjusted by blocking the exit ofadhesive material from desired areas of the applicator tip. In FIG. 6aand FIG. 6b, the applicator tips 40,50 are shown as being treated inportions to prevent adhesive from exiting the applicator tip in thetreated areas. FIG. 6a represents a hollow dome-shaped applicator tip,whereas FIG. 6b represents a chisel-shaped applicator tip having grooves54 formed in the flat surfaces thereof. In each of these embodiments,the areas 45,55 (shown in the Figures using stippling) of the applicatortip are treated or coated so as to block exit of the adhesive material,such that the material does not exit to the surface of the applicatortip. In these embodiments, the adhesive material will thus be forced toproceed through the applicator tip and exit only in the desired areas.

In these embodiments, any suitable treatment or coating material may beused to treat or coat the otherwise exposed surfaces of the applicatortip to prevent adhesive material from exiting in those areas. Forexample, the applicator tip can be coated by a cured form of theadhesive material, other cured or curable polymeric materials, materialsthat provide barrier properties upon setting, or the like. Likewise, anysuitable material may be coated upon the desired surface of theapplicator tip, which provides the desired blocking characteristics tothe applicator tip. For example, suitable solid, semi-solid, or liquidparticles can be directly applied to the applicator tip surface, or canbe dispersed in a suitable coating material (such as a solvent,dispersant or the like) and coated onto the applicator tip. For example,acceptable results can be obtained by dissolving polymeric materials,such as butyrate, in a suitable solvent, such as acetone, and coatingthe resultant solution onto the desired portions of the applicator tip.As a further example of the above, suitable materials such as paints,sealants, or the like can be applied onto the desired portions of theapplicator tip to provide the adhesive blocking property.

Alternatively or in addition, the treatment can include any suitablemethod that alters the properties of the surface of the applicator tip.For example, heating, melt smearing, ultrasonic welding, spray coatingor the like can be used at the desired portions of the tip so as toclose the pores in that area. Likewise, a suitable material can beapplied to the applicator tip to close the pores. For example, applyinga suitable solvent, such as acetone or the like, can close the pores ofthe applicator tip.

Preferably, such treatment affects only the surface of the applicatortip, or only to a small depth of the applicator tip, so as not to plugthe applicator tip or otherwise render it inoperable.

In alternative embodiments, shown in FIGS. 6c and 6 d, the applicatortips 40,50 are shown as being covered in portions by a separatecomponent that prevents adhesive from exiting the applicator tip in thecovered areas. FIG. 6c represents a hollow dome-shaped applicator tip,whereas FIG. 6d represents a chisel-shaped applicator tip having grooves54 formed in the flat surfaces thereof. In each of these embodiments,areas of the applicator tip are covered with a separate component orcover 46,56 to block exit of the adhesive material, such that anyadhesive material that exits to the surface of the applicator tip is notexposed to the environment. In these embodiments, the bulk of theadhesive material will thus be forced to proceed through the applicatortip and exit only in the desired areas.

In these embodiments, the cover 46,56 is a separate component, which canbe applied to the applicator tip as part of the manufacturing process,or can be applied to the applicator tip by the user prior to use. Thecover 46,56 can be attached to the applicator tip by any suitable means.

As used herein, the terms “attach” or “attached” as referring to theapplicator tip means operably connecting the applicator tip to theapplicator body, or parts thereof, directly or through other components.Thus, for example, the applicator tip can be attached to the applicatorbody in any suitable way, including but not limited to mechanicalarrangements such as luer locks, threads or locking rings, pressureand/or friction fitting, adhesive or chemical arrangements such asadhesive or chemical bonding, heat-shrink attachment, ultrasonicwelding, and the like.

For example, the cover can be adherently bonded to the applicator tip,can be attached to the applicator tip by heat-shrinking the cover ontothe applicator tip, can be screwed onto the applicator tip by suitablethreads or locking rings (not shown) or can be held to the applicatortip by pressure and/or friction. Adherent or heat-shrink attachment maybe preferred in embodiments where the cover is not to beinterchangeable, or where the cover is attached during the manufacturingprocess. However, screw, locking or friction/pressure attachment may bepreferred in embodiments where interchangeability is desired, such aswhere different sizes or types of covers are available. Suchinterchangeable tips can be used, for example, to provide differentdegrees of coverage of the applicator tip or to alter the profile ofapplication of the adhesive material.

In these embodiments, any suitable material may be used to form thecover, which in turn covers the otherwise exposed surfaces of theapplicator tip to prevent adhesive material from exiting in those areas.For example, the covers can be made from natural materials such ascellulose, cardboard, metal, ceramic, plastics such as butyrate or highdensity polyethylene, polypropylene, polyester, or the like.Alternatively, the cover can be formed from the tip material itself,such as from the surface layer of the tip material, such as by theabove-described processes.

In FIGS. 6a-6 d, the applicator tip is shown as having a hollow centralinterior portion of the applicator tip 40,50, as shown by dashed lines42,52. As described above, however, such design is optional, and can bepresent or not, as desired.

In embodiments of the present invention, the applicator tip material canbe either porous or solid. By porous materials are meant those throughwhich the adhesive material can flow through, such as by passing throughpores of the material. By non-porous or solid materials are meant thosethrough which the adhesive material cannot flow, either because thereare no pores, or because the pores are so small that the material iseffectively non-porous. Travel of the adhesive material through thesolid materials would thus be by way of the sectionings made accordingto the present invention.

In other embodiments of the present invention, the applicator tip can beformed using a combination of materials that are porous, such asdescribed above, and non-porous, or substantially non-porous withrespect to the material to be applied using the applicator tip. Forexample, the applicator tip in embodiments may be formed with one ormore sections of non-porous or substantially non-porous material, andone or more sections of porous material. In such embodiments, thenon-porous (or substantially non-porous) section generally prevents flowof material through the section, while the porous section permits flowthrough the section. In this manner, the flow of material through theapplicator tip can be controlled. Such control can, for example, provideprecise flow control to enable placement of the material exiting theapplicator tip in a fine line and/or at precise locations.

For example, FIGS. 14a and 14 b show top-down views of applicator tips.The applicator tips each include a non-porous section 92 that surroundsa porous section 94. As shown and as will be apparent, the placement ofthe porous section or sections within the non-porous section or sectionscan be symmetrical, as in FIG. 14a, or non-symmetrical, as in FIG. 14b.FIGS. 15a and 15 b show elevational views of the applicator tips shownin FIGS. 14a and 14 b, respectively.

Preferably, in these embodiments, the porous section(s) and thenon-porous sections(s) are coextensive in a fluid-flow direction throughthe applicator tip. That is, for example, it is preferred that theporous section(s) extend entirely through the applicator tip, to permitexpression of the desired material through the applicator tip. However,if desired, the non-porous section(s) can be altered to alter the fluidflow through the applicator tip, such as by providing a small exposurewithin the applicator tip, but increasing through the applicator tip toa small porous section. This is shown, for example, in FIG. 15c, wherethe porous member 94 starts out with a larger area, to permit easyuptake of material, but narrows to a smaller area to permit preciseplacement of the material. The non-porous section 92 likewise starts ata small area, but enlarges consistent with the narrowing of the poroussection 94.

In these embodiments, any suitable non-porous material can be used, suchthat the material is non-porous, or substantially non-porous withrespect to the material to be applied using the applicator tip. Suitablenon-porous materials include, but are in no way limited to,polyethylenes such as low density polyethylene and high densitypolyethylene, as well as other non-porous materials.

According to the present invention, the applicator can be attached to asuitable applicator body, such as a tube, in any suitable way. Forexample, the applicator tip can be attached to an end of the applicatorbody by annealing, bonding or form-fitting the applicator tip into oronto an opening in the applicator body. In embodiments of the presentinvention, the applicator tip can be attached to the applicator bodyusing a luer lock configuration. Luer lock configurations provide abenefit of being able to change the applicator system, such as changingthe design of the applicator tip, without the resulting need to redesignthe entire product configuration. That is, by providing a Luer lockmechanism on the applicator body, any of various applicator tips cansubsequently be applied to the applicator body.

According to this aspect of the present invention, the luer lockconnector can also provide the desired effect of channeling the adhesivematerial toward a desired external surface application subportion of theapplicator tip, such as the distal end of the applicator tip. This canbe accomplished because a portion of the applicator tip can be hollowedout to accept the luer lock connector. Thus, as the adhesive materialflows through the luer lock connector, it flows through further towardthe application subportion before actually entering the material of theapplicator tip. Accordingly, the luer lock can provide the double effectof providing a means of attaching the applicator tip to the applicatorbody, and providing shorter flow path lengths of the adhesive throughthe material of the applicator tip.

When used, the luer lock connection can be made in any desiredconfiguration. Suitable constructions of the luer lock mechanism areshown in non-limiting fashion in FIGS. 7a-c. FIG. 7a shows an exemplaryapplicator body 20 having attached to one end a cap 60 having a maleluer lock connector 62. The cap 60 can be made of any suitable material,such as the same materials that are used to form the applicator body 20.A corresponding female luer lock connector 64 is supported in a tipretainer and support member 63, as shown in FIG. 7b. The tip retainerand support member or platform 63 can be formed in any configuration asdesired, but are depicted as having an open area into which theapplicator tip can be placed. Such a platform could be formed, forexample, by injection molding the platform around an applicator tip, byforming the applicator tip around a preformed platform, or by attachinga preformed applicator tip to a preformed platform. Preferably, as shownin FIG. 7b, the applicator tip 70 includes a hollow area or void 72,suitable for receiving the female luer lock connector 64 when the tipretainer and support member 63 is mated with the applicator tip. Oncemated, the components form a unitary component, as shown in FIG. 7c.

The applicator tip bearing the luer lock connector can then be attachedto the applicator body bearing a corresponding luer lock connector, toform a complete applicator device, as shown in FIG. 8. Of course,although this embodiment has been described herein as the applicatorbody having a male luer lock connector and the applicator tip as havinga female luer lock connector, the invention is not so limited. Rather,these connectors can be reversed, as desired.

Although all of the above-described embodiments provide improved flowproperties and improved flow control for applying the material from theapplicator, still further improvements can be made. In particular,according to the present invention, the flow properties and flow controlcan be further improved by providing an applicator tip that issectioned. As used herein, the term “sectioned” refers to the applicatortip as having been cut one or more times to provide an apparentplurality of sections in the applicator tip. Such cuts can be completelythrough the applicator tip, resulting in several distinct parts, or thecuts can be only partially through the bulk portion of the applicatortip, such that the applicator tip remains as a unitary part. Preferably,for ease of handling and manufacture, the cuts are not made completelythrough the bulk material.

An example of a sectioned applicator tip according to the presentinvention is shown as an enlarged scale, cross-sectional view in FIG. 9.FIG. 9 shows the applicator tip 80 as being inserted into a containerbody 82. The applicator tip 80 is sliced or sectioned by one or morecuts, shown in FIG. 9 as cuts (dashed lines) 84. Although FIG. 9 showsthe cuts as extending to slightly below the end of the container body,the depth of the cuts can be any depth that may be desired. As shown inFIGS. 10a-10 d, the cuts can extend only slightly into the applicatortip and not into the area defined by the container body (FIG. 10a); thecuts can extend down to about the point where the container body ends(FIG. 10b); or the cuts can extend through the applicator tip into thearea defined by the container body, to any distance up to the end of theapplicator tip (FIG. 10c). Furthermore, multiple cuts in the sameapplicator tip can extend different distances, as desired. For example,FIG. 10d shows cuts in the central portion as extending further thancuts in an outer portion of the applicator tip.

In embodiments of the present invention, the location of the cuts orsectionings can be in any desired form. For example, in FIG. 9, thesection cuts are depicted as being parallel to each other. However, thesectioning cuts need not be parallel, and can instead be non-parallel oreven intersecting. For example, FIGS. 11a-11 b depict top-down views ofthe applicator tip using alternative sectioning cuts. FIG. 11a showsthree section cuts, made generally according to that shown in FIG. 9.FIG. 11b shows four section cuts, made to substantially intersect at thedistal end of the tip. Of course, numerous other configurations of thesectioning cuts can be made, depending on the desired flowcharacteristics of the material to be applied.

In embodiments of the present invention, the cuts or sectionings canextend through an entire width, depth and/or length of the applicatortip material, or they can extend only a portion of such dimension. Forexample, FIGS. 11a and 11 b show the cuts as extending across a fullwidth or length of the applicator tip material. However, as shown inFIG. 12, the cuts can extend across only a portion of the dimension. Forexample, FIG. 12 shows the cuts or sectionings 84 as not fully reachingthe outer circumference of the applicator tip 80.

In embodiments, the sectioning can be made by forming channels orpassageways, rather than in the form of discrete cuts. For example, thesectioning can be in the form of one or more channels cuts through theapplicator tip material. This construction of the sectioning isparticularly suitable for applicator tips made from materials that arenon-porous, or substantially non-porous with respect to the material tobe applied using the applicator tip. For example, FIGS. 13a and 13 bdepict applicator tips where the sectioning is formed as one or morechannels 85 formed in the applicator tip material 80. The channels canbe formed in any suitable size or shape as desired to accommodateapplication of the material.

Furthermore, although the sectioning has been shown with respect to asolid, dome-shaped cylindrical applicator tip, the invention is notlimited to such embodiments. Rather, the sectioning of the presentinvention can be applied to any or all of the various applicator tipdesigns described above, including those that have hollowed out innerareas, surface grooves, covers, or the like, those that are of differentshapes such as chisels, and those that have extension portions at thedistal end of the applicator tip.

When the section cuts are to be used, the cuts may be made by anyconventional means including by a knife, saw, drill, borer, or the like.Alternatively, the cuts can be made by initially forming them in thematerial during the tip manufacturing process, such as by molding or thelike.

Preferably, the number and location of the section cuts are sufficientto alter the flow properties of the material through the applicator tip.According to embodiments of the present invention, the number of cutscan be from as low as 1 to as many as will effectively be accommodatedby the applicator tip. The number of cuts can thus range, for example,from 1, 2, 3, 4 or 5 or more, to 5, 10 or 15 or more, or any value inbetween.

According to the present invention, the applicator can include anysuitable adhesive material. The adhesive material can include monomeric(including prepolymeric) materials, polymeric materials, or mixturesthereof. The monomer (including prepolymeric) adhesive composition mayinclude one or more polymerizable monomers. Preferred adhesivecompositions for use in applicators of the present invention are usefulas tissue adhesives, sealants for preventing bleeding or for coveringopen wounds, and in other biomedical applications. They find uses in,for example, apposing surgically incised or traumatically laceratedtissues; retarding blood flow from wounds; dressing burns; dressing skinor other superficial or surface wounds such as compromised skin or othertissue (such as abrasions, chaffed or raw skin, minor cuts and scrapes,sores and/or ulcers such as stomatitis); protecting intact skin; andaiding repair and regrowth of living tissue. Adhesive compositions ofthe present invention are also useful in industrial and homeapplications, for example in bonding rubbers, plastics, wood,composites, fabrics, and other natural and synthetic materials.

Preferred monomers that may be used in this invention are readilypolymerizable, e.g. anionically polymerizable or free radicalpolymerizable, or polymerizable by zwitterions or ion pairs to formpolymers. Such monomers include those that form polymers, that may, butdo not need to, biodegrade. Such monomers are disclosed in, for example,U.S. Pat. No. 5,328,687 to Leung, et al., which is hereby incorporatedin its entirety by reference herein.

Particularly preferred adhesive materials are 1,1-disubstituted ethylenemonomers including, but not limited to, monomers of the formula:

HRC═CXY  (I)

wherein X and Y are each strong electron withdrawing groups, and R is H,—CH═CH₂ or, provided that X and Y are both cyano groups, a C₁-C₄ alkylgroup. Examples of monomers within the scope of formula (I) includeα-cyanoacrylates, such as ethyl, butyl, and/or 2-octyl cyanoacrylate,vinylidene cyanides, C₁-C₄ alkyl homologues of vinylidene cyanides,dialkyl methylene malonates, acylacrylonitriles, vinyl sulfinates andvinyl sulfonates of the formula CH₂═CX′Y′ wherein X′ is —SO₂R′ or —SO₃R′and Y′ is —CN, —COOR′, —COCH₃, —SO₂R′ or —SO₃R′, and R′ is H orhydrocarbyl.

Furthermore, the adhesive composition contained in the applicator canfurther include various additives as are known in the art, including butnot limited to flavorants, preservatives, plasticizing agents,stabilizing agents, formaldehyde concentration reducing agents, pHmodifiers, thickening agents, cross-linking agents, fibrousreinforcement agents, colorants, and the like.

Suitable compositions, methods of making such compositions, and methodsfor incorporating such compositions into a dispenser device aredescribed, for example, in U.S. Pat. No. 5,928,611 to Leung; U.S. Pat.Nos. 5,328,687, 5,514,371, 5,514,372, 5,575,997, 5,582,834 and5,624,669, all to Leung et al; U.S. Pat. No. 5,259,835 to Clark et al.;U.S. Pat. No. 3,527,841 to Wicker et al.; U.S. Pat. No. 3,722,599 toRobertson et al.; U.S. Pat. No. 3,995,641 to Kronenthal et al.; and U.S.Pat. No. 3,940,362 to Overhults; and U.S. patent applications Ser. Nos.08/266,647, 08/714,288, 09/099,457, 09/430,177, and (No. 100497.02 filedOct. 29, 1999), the entire disclosures of which are incorporated hereinby reference.

According to the present invention, the applicator tip may, but neednot, include a polymerization and/or cross-linking initiator and/or ratemodifier, such as an accelerator or inhibitor, for a polymerizablemonomer adhesive material contained in the applicator. Suitablepolymerization and/or cross-linking initiators and rate modifiers, andmethods for applying them to the applicator tip, are described in, forexample, U.S. Pat. No. 5,928,611 and U.S. patent application Ser. No.09/430,177, filed Oct. 29, 1999, Ser. Nos. 09/430,176, 09/430,289,09/430,290, and 09/430,180 filed Oct, 29, 1999; Ser. No. 09/343,914filed Jun. 30, 1999; Ser. No. 09/385,030 filed Aug. 30, 1999; and Ser.No. 09/176,889 filed Oct. 22, 1998, the entire disclosures of which areincorporated herein by reference. Preferred initiators for some medicaluses include benzalkonium chloride, and for some industrial uses includedimethyl toluidine.

In embodiments of the present invention where a polymerization and/orcross-linking initiator and/or rate modifier, or other material, isincluded in the applicator tip, the material can be included in theapplicator tip in any suitable or desirable manner. For example, thematerial may be loaded in the tip, such that it is loaded in pores orinterstices of the applicator tip material, and/or the material may bechemically or physically attached to the applicator tip material,whether on exterior or interior surfaces thereof. In embodiments, thematerial can also be loaded in the applicator tip in proximity to thesectionings or cuts. For example, the material may be chemically orphysically attached to the applicator tip material on exposed surfacesaround the sectionings or cuts, such as being chemically or physicallyattached to the exposed surfaces of channels formed in the applicatortip. This latter approach is particularly suitable for solid applicatortips, where pores do not exist, or where pores do exist but aresubstantially inaccessible by the adhesive material to be applied.

The polymerization and/or cross-linking initiator and/or rate modifiermay be applied to the applicator tip by any suitable means, including,but not limited to, spraying, dipping, injecting, or brushing theapplicator tip with a liquid medium containing the polymerization and/orcross-linking material. It is preferably applied to the tip by dippingor injecting. For example, it may be applied to the tip by pumping ofthe liquid medium, for example, through a syringe, onto the distal endof the applicator tip.

The polymerization and/or cross-linking initiator and/or rate modifiermay be applied to porous applicator tips by using a vacuum or pressureprocess. In each process, a solution or suspension of the polymerizationand/or cross-linking initiator and/or rate modifier is introduced into avacuum or pressure chamber. The applicator tips, either individually orpreferably in batches, are placed into the solution or suspension in thepressure vessel in a manner such that the applicator tips preferably donot float to the top of the solution or suspension. For example, theapplicator tips can be placed in the solution or suspension in a wirebasket or other suitable container, which would hold the applicator tipsunder the solution or suspension, or a wire mesh or other suitableretainer could be placed over the applicator tips to dunk or sink theminto the solution or suspension. Once the applicator tips are in thesolution or suspension, the vessel can be sealed and an appropriatevacuum or pressure applied.

Application of the vacuum or pressure results in air that is trapped inthe applicator tips being degassed, or forced out of the applicatortips, and being replaced by the solution or suspension. This replacementof air by the solution or suspension thereby loads the material onto orinto the applicator tips. The end of the degassing phase can be observedby the absence of newly formed air bubbles. After a desired treatmenttime, the vacuum or pressure in the vessel can be released, and thetreated applicator tips can be removed.

In exemplary embodiments, preparing an applicator for dispensingpolymerizable monomeric compositions includes applying a material to asuitable applicator tip, such as a porous polyethylene, foam or fibroustip, which is attached to an applicator body, such as a butyrateapplicator tube or other suitable holder.

When the applicator is intended to contain an amount of polymerizablemonomeric composition, the applicator body or tube may comprise aconduit or reservoir for the polymerizable monomeric composition. Inthis embodiment, the applicator tip may be operably connected to theconduit or reservoir, such as by being fitted on an open end of theconduit, so that fluid flowing through the conduit also flows throughthe applicator tip.

In addition to the polymerization and/or cross-linking initiator and/orrate modifier, the applicator tip can also include various othermaterials that may or may not act as a polymerization initiator and/orrate modifier. For example, the applicator tip can include a flavorant,such that it imparts a flavor to the adhesive material when the adhesivematerial is applied to a surface. Incorporation of a flavorant isparticularly preferred, for example, when the cyanoacrylate adhesivematerial is to be applied to oral surfaces, such as to treat ulcers suchas stomatitis or cold sores. Similarly, the applicator tip can include abioactive material, which may or may not also be a polymerization and/orcross-linking initiator and/or rate modifier. Examples of suitablebioactive materials include, but are not limited to, medicaments such asantibiotics, antimicrobials, antiseptics, bacteriocins, bacteriostats,disinfectants, steroids, anesthetics, antifungal agents,anti-inflammatory agents, antibacterial agents, antiviral agents,antitumor agents, growth promoting substances, antioxidants, or mixturesthereof.

The applicator tip may be composed of any of a variety of materialsincluding polymerized materials such as plastics, foams, rubber,thermoset resins, films, fibers, or membranes. Where foams are used inthe applicator tip, the foam can be either an open-celled form, aclosed-cell foam, or a mixture thereof. Any suitable foam material canbe used and suitable foams include, for example, thermoplasticpolyurethane foam, preferably a soft, absorbent thermoplasticpolyurethane foam.

In embodiments, the applicator tip may be made from polyurethane,polyesters, polyolefins such as polyethylene, or polyamides. Inembodiments, the applicator may be made from polyethylene, such as thatsold by Porex Technologies Corp. (Fairbum, Ga.) under the trademarkLabPor®. In embodiments, the applicator tip can also be made fromfibers, either natural or synthetic, such as cotton, rayons, nylons, andmixtures thereof. Additionally, the applicator tip may be composed ofmaterials such as metal, glass, paper, ceramics, and the like. Theapplicator tip material may be porous, absorbent, or adsorbent in natureto enhance and facilitate loading of a material on or in the applicatortip. For example, the porous applicator tip may be composed of amaterial having random pores, capillaries, a honeycomb material, amaterial having a woven pattern, etc. The degree of porosity will dependon the materials being used, and can be determined by one of ordinaryskill in the art without undue experimentation. Porosity is the openvolume within the pores of an applicator tip divided by the total volumeof the applicator tip.

In embodiments, the applicator tip may be porous and have an averagepore size of about 1 μm to about 500 μm. Generally, according to thepresent invention, an applicator tip having an average pore size ofabout 1-100 μm such as 10-30 is used with a polymerizable materialhaving a viscosity of about 1-30 cP, preferably about 2-18 cP, and morepreferably 5-7 cP at 25° C. An applicator tip having an average poresize of from about 1 μm to about 100 μm is preferably used with apolymerizable material having a viscosity of about 10-30 cP. When thepolymerizable and/or cross-linkable material has a viscosity higher than7 cP, the average pore size of the applicator tip is generallyincreased. For example, an applicator tip having an average pore size ofabout 40-300 μm such as 60-125 μm is preferably used with apolymerizable material having a viscosity of about 30-500 cP, preferablyabout 35-350 cP, and more preferably about 50-200 or 60-140 cP at 25° C.In embodiments, an applicator tip has a pore volume of less than orequal to 80 percent, preferably between 20-60 percent.

In embodiments of the present invention, the adhesive composition has aviscosity of about 1-5000 centipoise, preferably 1-600 centipoise, morepreferably 1-100 or 2-50 centipoise such as 2-18, 2-10 or 5-7centipoise, or 30-500 such as 50-100 or 100-200 centipoise at 25° C. Theviscosity can be selected according to the proposed use—e.g., 1-100centipoise for certain uses and 100-200 centipoise for other uses.Additionally, the composition may be a gel, e.g., 50,000-500,000centipoise at 25° C. Such gels are particularly advantageous inembodiments of the present invention, because the gels are more easilyexpelled through the applicator due to the decreased resistance totravel through the applicator tip provided by the present invention. Theviscosity of the adhesive composition can be measured with a BrookfieldViscometer. Additionally, in embodiments where a sterilization treatmentis applied, the viscosity of the composition should preferably bemaintained or increased by a controlled and acceptable amount aftersterilization.

The applicator tip according to the present invention, where it connectsto the applicator tube, may have an elongated tubular portion, out ofwhich the mixed polymerizing and/or cross-linking material is expelled.A portion of the applicator tip that is immediately downstream of theapplicator tube is advantageously porous in order to avoid a sharppressure drop and ensure a constant mixed ratio profile. The structurecan preferably trap fragments of any barriers or materials used toseparate one or more components within the applicator container so thatthey will not clog the device or contact the patient or surface ontowhich the adhesive is being applied.

When using a porous applicator tip to apply the adhesive composition,the composition preferably is not expressed directly through theapplicator tip in a continuous motion. According to embodiments of thepresent invention, the adhesive composition is (1) expressed to the endor part way to the end of the applicator tip, (2) the pressure isreleased to draw the composition back into the applicator, and (3) thecomposition is then subsequently expressed through the applicator tip ina continuous motion. This is called a suck-back method of applying theadhesive composition of the present invention. When used with a tip thatbears an initiator, this method lets the adhesive composition polymerizebetter than if it had been expressed directly through the tip.

According to the present invention, the applicator can be manufacturedin any of various ways, generally known in the art. For example, anapplicator tube can be sealed at one end, and a frangible vialcontaining the monomeric adhesive material can be placed in theapplicator tube. The remaining open end of the applicator tube can thenbe sealed by filling it with the applicator tip, which can be bonded orform-fit into the opening in the applicator tube. Such applicator tipcan be previously prepared to incorporate the polymerization initiatoror rate modifier, or the polymerization initiator or rate modifier canbe applied to the applicator tip subsequent to placing the applicatortip on the applicator. Furthermore, if desired, a second applicator tip,of the same or different design or configuration as the first applicatortip, can be affixed at the opposite end of the applicator tube ratherthan sealing the applicator tube. Such second applicator tip can havethe same of different constructions as those described above.

However, the present invention further provides an alternative means forforming the applicator assembly. According to embodiments of the presentinvention, the applicator tip can be first applied to an open end of theapplicator body, and the polymerization initiator or rate modifier canbe applied to the applicator tip through the length of the applicatorbody. Once the initiator is applied, the frangible vial can be insertedinto the applicator body, and then the remaining open end of theapplicator body can be sealed.

According to this embodiment of the present invention, the applicatortip is first applied to an open end of the applicator body. Theapplicator tip can be applied to the applicator body by any suitablemethod, as described above. Next, the polymerization initiator or ratemodifier is applied to the applicator tip. The polymerization initiatoror rate modifier can be applied, for example, by dispensing the materialonto the back (inside or proximal) end of the applicator tip, forexample, by using a standard dispensing nozzle or injection syringe.

Once the polymerization initiator or rate modifier has been applied tothe applicator tip, the frangible vial containing the monomeric adhesivematerial can be inserted into the applicator tube. In this manner, thefrangible vial can rest up against the back end of the applicator tip.

Next, the remaining open end of the applicator body is sealed. Thesealing can be affected by any suitable means known in the art. Forexample, the applicator tube can be sealed by heat, the open end can becovered, for example by a cap, or the like. Where a separate cap is usedto seal the applicator body, it is preferred that the cap is bonded tothe applicator body, for example by ultrasonic welding, chemicalbonding, physical bonding (such as adhesive), or the like.

Once the applicator assembly is prepared, the assembly (or individualcomponents thereof) can be sterilized according to known practices.Compatibility of the adhesive composition and the applicator with one ormore sterilization procedures is preferred in embodiments of the presentinvention because many uses of the adhesive compositions, such as manysurgical and other medical applications, require sterilized products. Inpreferred embodiments, there is substantially no initiation ofpolymerization of monomeric liquid adhesive compositions that affectsthe utility of the monomer or monomers caused by the sterilizationprocess.

Sterilization of the monomer composition and/or its packaging can beaccomplished by techniques known to the skilled artisan, and ispreferably accomplished by methods including, but not limited to,chemical, physical, and/or irradiation methods. Examples of chemicalmethods include, but are not limited to, exposure to ethylene oxide orhydrogen peroxide vapor. Examples of physical methods include, but arenot limited to, sterilization by heat (dry or moist) or retort canning.Examples of irradiation methods include, but are not limited to, gammairradiation, electron beam irradiation, and microwave irradiation. Apreferred method is electron beam irradiation. In embodiments where acomposition is to be used for medical applications, the sterilizedcomposition must show low levels of toxicity to living tissue during itsuseful life.

While the invention has been described with reference to preferredembodiments, the invention is not limited to the specific examplesgiven, and other embodiments and modifications can be made by thoseskilled in the art without departing from the spirit and scope of theinvention.

What is claimed is:
 1. An article of manufacture for dispensing adhesivematerial, comprising: a container body and a porous applicator tip, andan adhesive material located in said container body in a non-contactingrelationship with said applicator tip prior to dispensing said adhesivematerial, wherein said applicator tip has a proximal end that isattached to said container body and a distal end located away from saidcontainer body, and wherein one or more cuts are made in said applicatortip to alter flow properties of said adhesive material through saidapplicator tip.
 2. The article of claim 1, wherein the one or more cutsextends only partially through said applicator tip.
 3. The article ofclaim 1, wherein the one or more cuts extends completely through saidapplicator tip.
 4. The article of claim 1, wherein the one or more cutsextends through said applicator tip to a portion of said applicator tiplocated within said container body.
 5. The article of claim 1, whereinthe one or more cuts extends through said applicator tip only to aportion of said applicator tip located outside said container body. 6.The article of claim 1, comprising a plurality of said cuts.
 7. Thearticle of claim 6, wherein said plurality of cuts are parallel to eachother.
 8. The article of claim 6, wherein said plurality of cuts are notparallel to each other.
 9. The article of claim 6, wherein at least twoof said plurality of cuts intersect each other.
 10. The article of claim9, wherein said at least two cuts intersect each other at about saiddistal end.
 11. The article of claim 1, wherein said porous applicatortip has a polymerization or cross-linking initiator or rate modifier forsaid adhesive material disposed thereon or therein.
 12. The article ofclaim 1, wherein said applicator tip is a non-porous applicator tip. 13.The article of claim 12, wherein said one or more cuts is formed as oneor more channels through said applicator tip.
 14. The article of claim13, wherein said applicator tip has a polymerization or cross-linkinginitiator or rate modifier for said adhesive material disposed onexposed surfaces of said channels.
 15. The article of claim 1, whereinsaid applicator tip is a porous applicator tip and is configured toprovide a flow path length ratio, A/B, of less than 1.5, wherein Brepresents a length of a shortest flow path of said adhesive materialthrough a material of the applicator tip to an external surface of saidapplicator tip adjacent said container body, and A represents a lengthof a shortest flow path of said adhesive material through the materialof the applicator tip to a predetermined application subportion of saidapplicator tip.
 16. The article of claim 15, wherein A/B is less than1.3.
 17. The article of claim 15, wherein A/B is less than
 1. 18. Thearticle of claim 15, wherein A/B is about
 1. 19. The article of claim15, wherein said predetermined subportion is said distal end.
 20. Thearticle of claim 1, wherein said applicator tip is hollow.
 21. Thearticle of claim 1, wherein said adhesive material is a syntheticpolymerizable or cross-linkable monomer material.
 22. The article ofclaim 1, wherein said applicator tip has a polymerization orcross-linking initiator or rate modifier for said adhesive materialdisposed thereon or therein.
 23. The article of claim 1, wherein saidadhesive material comprises 1,1-disubstituted ethylene monomers.
 24. Thearticle of claim 1, wherein said adhesive material comprisesα-cyanoacrylate monomers.
 25. The article of claim 1, wherein saidadhesive material has a viscosity of at least 60 cP at 25° C.
 26. Thearticle of claim 1, wherein a shape of said applicator tip is selectedfrom the group consisting of dome, conical, cylindrical, chisel andpolygonal shapes.
 27. The article of claim 1, wherein said proximal endof said applicator tip is curved.
 28. The article of claim 1, whereinsaid applicator tip is in a shape of a hollow dome.
 29. The article ofclaim 1, wherein said applicator tip comprises a polymerized material.30. The article of claim 1, wherein said applicator tip comprises aplastics material.
 31. The article of claim 1, wherein said applicatortip is absorbent or adsorbent.
 32. The article of claim 1, comprising acover surrounding at least a part but not all of an area of saidapplicator tip extending out of said container body.
 33. The article ofclaim 32, wherein said cover prevents said adhesive material fromexiting said applicator tip at said covered area, while permitting saidadhesive material to exit said applicator tip at an uncovered area. 34.The article of claim 32, wherein said cover is attached to saidapplicator tip.
 35. The article of claim 32, wherein said cover isattached to said container body.
 36. The article of claim 32, whereinsaid cover snugly matches contours of said applicator tip.
 37. Thearticle of claim 32, wherein said cover is a polymeric coating.
 38. Thearticle of claim 1, wherein the applicator tip is attached to thecontainer body by a luer lock.
 39. The article of claim 1, wherein saidadhesive material has a viscosity of 1-30 cP at 25° C.
 40. The articleof claim 1, wherein said adhesive material has a viscosity of 2-18 cP at25° C.
 41. A method of manufacturing the article of claim 1, comprising:forming said one or more cuts in said applicator tip; attaching theapplicator tip to the container body; dispensing a quantity of saidpolymerization or cross-linking accelerator or initiator for saidsynthetic or semi-synthetic material disposed thereon or therein, intosaid applicator tip; disposing said synthetic or semi-synthetic monomermaterial in said container body in a non-contacting relationship withsaid applicator tip; and sealing said container body.
 42. An article ofmanufacture for dispensing adhesive material, comprising: a containerbody and an applicator tip, and an adhesive material located in saidcontainer body in a non-contacting relationship with said applicator tipprior to dispensing said adhesive material, wherein said applicator tiphas a proximal end that is attached to said container body and a distalend located away from said container body, and wherein one or more cutsare made in said applicator tip to alter flow properties of saidadhesive material through said applicator tip, and further comprisingone or more grooves formed in the applicator tip that channel adhesiveexiting said applicator tip to said distal end of said applicator tip.43. The article of claim 42, wherein a shape of said applicator tip isselected from the group consisting of dome, conical, cylindrical, chiseland polygonal shapes.
 44. The article of claim 42, wherein said proximalend of said applicator tip is curved.
 45. The article of claim 42,wherein said applicator tip is hollow.
 46. The article of claim 42,wherein said applicator tip is in a shape of a dome.
 47. The article ofclaim 46, wherein said applicator tip is in a shape of a hollow dome.48. The article of claim 42, wherein said applicator tip is in a shapeof a chisel.
 49. The article of claim 48, wherein said one or moregrooves are formed on flat faces of said chisel shape.
 50. The articleof claim 42, comprising at least two grooves that are parallel to eachother.
 51. The article of claim 42, comprising at least two grooves thatare not parallel to each other.
 52. The article of claim 42, wherein theone or more cuts extends only partially through said applicator tip. 53.The article of claim 42, wherein the one or more cuts extends completelythrough said applicator tip.
 54. The article of claim 42, wherein theone or more cuts extends through said applicator tip to a portion ofsaid applicator tip located within said container body.
 55. The articleof claim 42, wherein the one or more cuts extends through saidapplicator tip only to a portion of said applicator tip located outsidesaid container body.
 56. The article of claim 42, comprising a pluralityof said cuts.
 57. The article of claim 56, wherein said plurality ofcuts are parallel to each other.
 58. The article of claim 56, whereinsaid plurality of cuts are not parallel to each other.
 59. The articleof claim 56, wherein at least two of said plurality of cuts intersecteach other.
 60. The article of claim 59, wherein said at least two cutsintersect each other at about said distal end.
 61. The article of claim42, wherein said applicator tip is a porous applicator tip.
 62. Thearticle of claim 61, wherein said porous applicator tip has apolymerization or cross-linking initiator or rate modifier for saidadhesive material disposed thereon or therein.
 63. The article of claim42, wherein said applicator tip is a non-porous applicator tip.
 64. Thearticle of claim 63, wherein said one or more cuts is formed as one ormore channels through said applicator tip.
 65. The article of claim 64,wherein said applicator tip has a polymerization or cross-linkinginitiator or rate modifier for said adhesive material disposed onexposed surfaces of said channels.
 66. The article of claim 42, whereinsaid applicator tip is hollow.
 67. The article of claim 42, wherein saidadhesive material is a synthetic polymerizable or cross-linkable monomermaterial.
 68. The article of claim 42, wherein said applicator tip has apolymerization or cross-linking initiator or rate modifier for saidadhesive material disposed thereon or therein.
 69. The article of claim42, wherein said adhesive material comprises 1,1-disubstituted ethylenemonomers.
 70. The article of claim 42, wherein said adhesive materialcomprises α-cyanoacrylate monomers.
 71. The article of claim 42, whereinsaid adhesive material has a viscosity of at least 60 cP at 25° C.
 72. Amethod of preparing an applicator tip suitable for dispensing asynthetic or semi-synthetic polymerizable or cross-linkable monomermaterial, comprising providing a porous applicator tip having a proximalend and a distal end, forming one or more cuts in said applicator tip toalter flow properties of said adhesive material through said applicatortip.
 73. The method of claim 72, wherein the one or more cuts extendsonly partially through said applicator tip.
 74. The method of claim 72,comprising a plurality of said cuts.
 75. The method of claim 74, whereinsaid plurality of cuts are parallel to each other.
 76. The method ofclaim 74, wherein said plurality of cuts are not parallel to each other.77. The method of claim 74, wherein at least two of said plurality ofcuts intersect each other.
 78. The method of claim 74, wherein said atleast two cuts intersect each other at about said distal end.
 79. Themethod of claim 72, further comprising attaching said applicator tip atsaid proximal end to a container body.
 80. The method of claim 79,further comprising disposing a synthetic or semi-synthetic polymerizableor cross-linkable monomer material in said container body.
 81. Themethod of claim 72, wherein said porous applicator tip has apolymerization or cross-linking initiator or rate modifier for saidadhesive material disposed thereon or therein.